US3137693A - Substituted pyrido [2, 3-e]-as-triazine 1-oxides - Google Patents
Substituted pyrido [2, 3-e]-as-triazine 1-oxides Download PDFInfo
- Publication number
- US3137693A US3137693A US171807A US17180762A US3137693A US 3137693 A US3137693 A US 3137693A US 171807 A US171807 A US 171807A US 17180762 A US17180762 A US 17180762A US 3137693 A US3137693 A US 3137693A
- Authority
- US
- United States
- Prior art keywords
- triazine
- oxide
- methylpyrido
- formula
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- RPZFHVGSZOZNCH-UHFFFAOYSA-N 1-oxidopyrido[2,3-e][1,2,4]triazin-1-ium Chemical class C1=CC=C2[N+]([O-])=NC=NC2=N1 RPZFHVGSZOZNCH-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 15
- -1 hydrazino, piperidino, morpholino, cyclohexylamino, phenethylamino, mercapto Chemical class 0.000 description 32
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical class NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 2
- WGTASENVNYJZBK-UHFFFAOYSA-N 3,4,5-trimethoxyamphetamine Chemical compound COC1=CC(CC(C)N)=CC(OC)=C1OC WGTASENVNYJZBK-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- YJSGNHSYRAKFFB-UHFFFAOYSA-N 2-methyl-1,1-dipropylhydrazine Chemical compound CCCN(NC)CCC YJSGNHSYRAKFFB-UHFFFAOYSA-N 0.000 description 1
- AFRXEIDHSZUAIC-UHFFFAOYSA-N 4-pyrido[2,3-e][1,2,4]triazin-3-ylmorpholine Chemical compound C1COCCN1C1=NN=C(C=CC=N2)C2=N1 AFRXEIDHSZUAIC-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000282461 Canis lupus Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- GCOWZPRIMFGIDQ-UHFFFAOYSA-N n',n'-dimethylbutane-1,4-diamine Chemical compound CN(C)CCCCN GCOWZPRIMFGIDQ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940117803 phenethylamine Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Definitions
- These compounds are crystalline solids useful as tranquilizers and antibacterial agents. When dispersed in water at a concentration of 50 parts per million, they inhibit the growth of bacteria such as Escherichia coli, Salmonella typhimurium and Staphylococcus aureas..
- All of the compounds, other than Where Y is mercapto, can be prepared by the reaction of two molecular proportions of a compound of the formula H-Y with one molecular proportion of a compound of the formula in an inert solvent such as chloroform at a temperature of O0 C.
- an inert solvent such as chloroform
- the reaction mixture is poured into ice-water, the product extracted with chloroform, the solvent evaporated and the residue purified by recrystalilzation from an organic solvent such as ethanol or a mixture of ethanol and water.
- the compounds wherein Y is mercapto are prepared by refluxing an alcoholic solution of two parts of thiourea and one part of a compound of the formula N @1 N N and thereafter separating the solid product formed followed by purification of said product by dissolution in aqueous alkali and reprecipitation with acetic acid.
- Example 1 3 diethylamin0pyrido[2,3 e] as triazine 1 0xide.--One-tenth mole of 3-chloropyrido[2,3-e]-as-triazine l-oxide was dissolved in 300 ml. of chloroform and cooled to 0 C. A solution of 0.21 mole of diethylamine in 120 ml. of chloroform was then added portionwise while maintaining the temperature below 10 C. After standing at 5 C. for one hour, the reaction mixture was poured into ice-water, the solid product which formed Was extracted with chloroform and the chloroform evaporated. The residue was purified by recrystallization from ethanol to obtain the desired product which melted at 124-125 C.
- Example 2 The reaction of 3-chloropyrido[2,3-e]-as-triazine l-oxide with piperidine in the same manner as that described in Example 1 produced 3-piperidinopyrido[2,3-e1-as-triazine l-oxide which melted at 116l17 C.
- Example 3 By substituting morpholine for the diethylamine of Example 1, there is obtained 3-morpholinopyrido[2,3-e1- as-triazine l-oxide melting at 169170 C.
- Example 4 The substitution of cyclohexylamine for diethylamine in Example 1 will produce 3-cyclohexylaminopyrido- [2,3-e1-as-triazine l-oxide which melts at -191 C.
- Example 5 Replacing diethylamine of Example I with phenethylamine results in the production of 3-phenethylaminopyrido[2,3-e]-as-triazine l-oxide which has a melting point of 174-175 C.
- Example 6 The reaction of n-butylamine with 3-chloropyrido- [2,3-e]-as-triazine l-oxide as described in Example 1 produces 3-n-butylaminopyrido[2,3-e1-as-triazine l-oxide melting at 174175 C.
- Example 7 The replacement of diethylamine of Example 1 with dimethylaminopropylamine readily fortms 3-dimethylaminopropylaminopyrido[2,3-e1-as-triazine l-oxide which melts at 250-251 C. with decomposition.
- Example 8 In the same manner as that described in Example 1, the reaction of hydrazine with 3-chloropyrido[2,3-e]-astriazine l-oxide will produce 3-hydrazinopyrido[2,3-e]- as-triazine l-oxide melting at 252-253 C. with decomposition.
- Example 9 Reacting sodium methoxide or sodium n-butoxide with 3-chloropyrido[2,3-e]-as-triazine l-oxide as described in Example 1 will produce 3-methoxypyrido[2,3-e] -as-triazine l-oxide and 3-n-butoxypyrido[2,3-e]-as-triazine l-oxide, respectively, the former of which melts at 149 C. with decomposition and the latter of which melts at 99-l00 C.
- Example 10 When 3-chloropyrido[2,3-e]-as-triazine l-oxide is reacted in the manner described in Example 1 with ethanol, isopropanol, dimethylamine, di-n-propylamine, methylamine, ethylamine, isopropylamine, diethylaminoethylamine, dipropylaminomethylamine or dimethylaminobutylamine there is obtained respectively, 3-ethoxypyrido[2,'3-e]-as-triazine l-oxide 3-isopropoxypyrido[2,3-e]-as-triazine 1-oxide 3-dimethylaminopyrido[2,3-e]-as-triazine l-oxide 3-di-n-propylaminopyrido [2,3-e] -as-triazine l-oxide -3-methylaminopyrido[2,3-e]
- Example 13 By following the procedure of Example 1, the reaction of a compound of the formula N N wherein R is ethyl, propyl, butyl, chloro, bromo, fluoro or iodo with a monoloweralkylamine, diloweralkylamine, lower alkanol, hydrazine, piperidine, morpholine, cyclohexylamine, phenethylamine, or diloweralkylaminoloweralkylamine will produce compounds of the formula wherein R is as defined above and Y is methylamino, ethylamino, propylamino, butylamino, dimethylamino, diethylamino, dipropylamino, dibutylamino, Inethoxy,
- the 3-chloro-7-R-pyrido[2,3-e]-as-triazine l-oxides employed as starting materials in the present invention can be prepared by refluxing two parts of guanidine and one part of a compound of the formula in a solvent such as t-butyl alcohol to form a compound of the formula which is heated on a steam bath with water in the presence of a catalyst such as potassium carbonate to obtain a compound of the formula A:NH2 N N which is thereafter reacted at about 20 C. with sodium nitrite in an acidified aqueous medium to obtain a con1- pound of the formula which is then refluxed with excess phosphorus oxychloride.
- a solvent such as t-butyl alcohol
- a catalyst such as potassium carbonate
- a compound of the formula I ta wherein R is a member of the group consisting of hydrogen, lower alkyl and halogen and Y is a member of the group consisting of monoloweralkylamino, diloweralkylamino, loweralkoxy, hydrazino, piperidino, morpholino, cyclohexylamino, phenethylamino, mercapto and diloweralkylaminoloweralkylamino.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US171807A US3137693A (en) | 1962-02-08 | 1962-02-08 | Substituted pyrido [2, 3-e]-as-triazine 1-oxides |
| GB4305/63A GB1023218A (en) | 1962-02-08 | 1963-02-01 | Substituted pyrido [2,3-e]-triazine 1-oxides |
| DEA42286A DE1188605B (de) | 1962-02-08 | 1963-02-08 | Verfahren zur Herstellung von Pyrido-[2, 3-e] [1, 2, 4]-triazin-1-oxyden |
| FR932768A FR2498M (fr) | 1962-02-08 | 1963-04-26 | Dérivés substitués d'oxyde-1 de pyrido (2,3-e)-triazine-as comme tranquillisants et agents antibactériens. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US171807A US3137693A (en) | 1962-02-08 | 1962-02-08 | Substituted pyrido [2, 3-e]-as-triazine 1-oxides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3137693A true US3137693A (en) | 1964-06-16 |
Family
ID=22625207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US171807A Expired - Lifetime US3137693A (en) | 1962-02-08 | 1962-02-08 | Substituted pyrido [2, 3-e]-as-triazine 1-oxides |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3137693A (fr) |
| DE (1) | DE1188605B (fr) |
| FR (1) | FR2498M (fr) |
| GB (1) | GB1023218A (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3453276A (en) * | 1966-10-06 | 1969-07-01 | Smithkline Corp | Triazinoindole compounds |
| US3549632A (en) * | 1969-01-13 | 1970-12-22 | American Cyanamid Co | 3-aminopyrido(4,3-e)-as-triazine and 3 - aminopyrido(4,3-e)-as-triazine-1-oxide |
| US4324786A (en) * | 1979-04-28 | 1982-04-13 | Egyt Gyogyszervegyeszeti Gyar | Pyrido[2,3-e]-as-triazine derivatives and pharmaceutical compositions |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2489355A (en) * | 1947-01-10 | 1949-11-29 | Merck & Co Inc | Benzotriazines |
-
1962
- 1962-02-08 US US171807A patent/US3137693A/en not_active Expired - Lifetime
-
1963
- 1963-02-01 GB GB4305/63A patent/GB1023218A/en not_active Expired
- 1963-02-08 DE DEA42286A patent/DE1188605B/de active Pending
- 1963-04-26 FR FR932768A patent/FR2498M/fr active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2489355A (en) * | 1947-01-10 | 1949-11-29 | Merck & Co Inc | Benzotriazines |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3453276A (en) * | 1966-10-06 | 1969-07-01 | Smithkline Corp | Triazinoindole compounds |
| US3549632A (en) * | 1969-01-13 | 1970-12-22 | American Cyanamid Co | 3-aminopyrido(4,3-e)-as-triazine and 3 - aminopyrido(4,3-e)-as-triazine-1-oxide |
| US4324786A (en) * | 1979-04-28 | 1982-04-13 | Egyt Gyogyszervegyeszeti Gyar | Pyrido[2,3-e]-as-triazine derivatives and pharmaceutical compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2498M (fr) | 1964-04-27 |
| DE1188605B (de) | 1965-03-11 |
| GB1023218A (en) | 1966-03-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2893992A (en) | I ii i i | |
| US3635982A (en) | Amino-substituted-quinoxalinyloxazolidines and -oxazines | |
| US3272811A (en) | Dihydrothieno-[3, 4-d]-pyrimidines | |
| US3137693A (en) | Substituted pyrido [2, 3-e]-as-triazine 1-oxides | |
| US2969372A (en) | Cycloalkylpyrazolo [3, 4-alpha] inden-4 [1h]-one derivatives | |
| US2963481A (en) | 6-pteridinecarboxylic acid esters | |
| CH630920A5 (de) | Verfahren zur herstellung neuer 6-aryl-s-triazolo-(4,3-a)-pyrido-(2,3-f)-1,4-diazepine. | |
| US3077473A (en) | Hydrazino-1, 2, 4-triazines | |
| Taylor et al. | Synthesis of Some [1, 2, 3] Thiadiazolo [5, 4-d] pyrimidines and Pyrimido [4, 5-b][1, 4] thiazines1 | |
| US2786845A (en) | Isomeric mixtures of 6-methyl-5-chloro-and 7-chloro-1, 2, 3, 4-tetrahydroquino-line derivatives | |
| US4066645A (en) | Derivatives of pyrazolo [1,5-a]pyrido[3,4-e]pyrimidine | |
| US3207660A (en) | Process for inhibiting growth of microorganisms | |
| US2393673A (en) | Substituted 4-amino benzoic acid | |
| US3418345A (en) | Halonitroanilides | |
| US3108102A (en) | 3-hydroxypyrido [2, 3-e]-as-triazine 1-oxide and related compounds | |
| US3375247A (en) | Heterocyclic compounds and methods for their production | |
| US3419563A (en) | Process for producing 7-amino-carbostyrile derivatives | |
| US2983727A (en) | 2-amino-4-[bis(2-haloethyl)amino] pyrimidines | |
| US2834780A (en) | Phthalidyl piperazines | |
| NO119797B (fr) | ||
| US2969371A (en) | Substituted indeno [1, 2-c] pyrazole derivatives | |
| US2749345A (en) | Pyrimidine compounds | |
| US2980678A (en) | Pyrimidines | |
| US3128273A (en) | 4-amino-pteridine-7-carboxamides and method of preparation | |
| US3249611A (en) | Novel method for the preparation of phthalazines |